Air-tolerant direct reductive N-methylation of amines using formic acid via simple inorganic base catalysis  

作　　者：Yan Huang Wei Deng Bo-Lin Lin 

机构地区：[1]School of Chemical and Environmental Engineering,Shanghai Institute of Technology,Shanghai 201418,China [2]School of Technology and Physical Science,ShanghaiTech University,Shanghai 201210,China

出　　处：《Chinese Chemical Letters》2020年第1期111-114,共4页中国化学快报（英文版）

基　　金：financial support by the National Natural Science Foundation of China (No.U1532135)

摘　　要：The construction of N-methyl amine moieties is an important reaction that has found numerous applications.Development of new methylation agents that are more environmentally benign than classical agents,such as iodomethane and methyl sulfate,is still highly desirable.Herein,we report a convenient protocol for direct reductive N-methylation of amines using formic acid as the methylation agent via simple inorganic base catalysis.The present protocol operates under transition-metal-free and air-tolerant conditions.Both the catalyst,K2 HPO4,and the reductant,polymethylhydrosiloxane(PMHS),are cheap and easily separable from the crude reaction product mixture.Mechanistic investigations suggest that the reaction occur through the formation of an acetal inte rmediate followed by the C-N bond formation.The construction of N-methyl amine moieties is an important reaction that has found numerous applications.Development of new methylation agents that are more environmentally benign than classical agents,such as iodomethane and methyl sulfate,is still highly desirable.Herein,we report a convenient protocol for direct reductive N-methylation of amines using formic acid as the methylation agent via simple inorganic base catalysis.The present protocol operates under transition-metal-free and air-tolerant conditions.Both the catalyst,K2 HPO4,and the reductant,polymethylhydrosiloxane（PMHS）,are cheap and easily separable from the crude reaction product mixture.Mechanistic investigations suggest that the reaction occur through the formation of an acetal inte rmediate followed by the C-N bond formation.

关 键 词：Air tolerant N-METHYLATION Formic acid Simple inorganic bas Transition-metal-free 

分 类 号：O621.251[理学—有机化学]